Hydrochloric Acid → 3-(2-Aminoethyl)-1-methylindolin-2-one hydrochloride

HRID 1749546Notes

Reaction equation

HRID 1749546 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][NH2:13])=[CH:3]1.CS(C)=[O:16].[ClH:18]>>[ClH:18].[NH2:13][CH2:12][CH2:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]1=[O:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 234921-Methyl-1H-indole-3-ethylamine

Product 1

HCID 529932843-(2-Aminoethyl)-1-methylindolin-2-one hydrochlorideYield 45%

Procedure

To a solution of 2-(1-methyl-1H-indol-3-yl)ethanamine (2.5 g cude) in DMSO (1.33 g, 17.0 mmol) was added concentrated hydrochloric acid (1.2 mL) slowly. The resulting reaction mixture was stirred at room temperature in a sealed reactor for 16 h. The reaction mixture was concentrated and the residue was purified by preparative HPLC to afford the title compound (1.5 g, 6.59 mmol, 45% yield over two steps) as a yellow solid. MS (ESI) m/z 191.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-610b76fe50b545fea3da60796d7a94e7
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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